Process for producing photographic film having a magnetizable layer thereon and such a photographic film

ABSTRACT

A process for producing a photographic film having thereon a magnetic recording layer by applying a dispersion of a magnetic substance to an antihalation layer of a light-sensitive film for cinema, where the dispersion contains a compound or compounds, having at least two or more isocyanato groups or thioisocyanato groups or the anti-halation layer is previously processed with a solution containing the compound. A photographic film where either the magnetic layer contains, or the antihalation layer has been processed with, such a compound or compounds.

United States Patent 1191 Yamamoto et al.

1 PROCESS FOR PRODUCING PHOTOGRAPHIC FILM HAVING A MAGNETIZABLE LAYER THEREON AND SUCH A PHOTOGRAPHIC FILM [75] Inventors: Nobuo Yamamoto; Hideo Kawaguchi; Katsuharu Furukawa, all of Minami Ashigara, Japan [73] Assignee: Fuji Photo Film Co., Ltd.,

Kanagawa, Japan [22] Filed: Apr. 24, 1973 [2]] Appl. No.: 354,055

[30] Foreign Application Priority Data Apr. 12, 1972 Japan 47-41123 [52] US. Cl 96/39, 96/84 R, 117/235, 117/239 [51] Int. Cl G03c 5/14, G03c 1/84, C22c 39/00 [58] Field of Search 96/84 R, 4, 39; 117/235, 117/239 [56] I References Cited UNITED STATES PATENTS 3,649,541 3/1972 lngersoll 117/235 Mar. 11, 1975 3,689,317 9/1972 Akaskietal 117/235 3,704,167 11/1972 Yamamoto et a1. 117/239 3,773,539 11/1973 Sato et a1. 96/84 R FOREIGN PATENTS OR APPLICATIONS 1,147,399 4/1963 Germany 117/235 Primary Examiner-Mary F. Kelley Attorney, Agent, or Firm-Sughrue, Rothwell, Mion, Zinn & Macpeak [57] ABSTRACT 21 Claims, No Drawings 1 PROCESS FOR PRODUCING PHOTOGRAPHIC FILM HAVING A MAGNETIZABLE LAYER THEREON AND SUCH A PHOTOGRAPHIC FILM BACKGROUND OF THE INVENTION 1. FIELD OF THE INVENTION The present invention relates to a process for producing photographic film having a magnetizable layer thereon and to such a film. More particularly, it relates to a process for providing on a movie film a sound track composed of a magnetic substance and to such a movie film.

2. DESCRIPTION OF THE PRIOR ART As processes to provide a sound track on a movie film, there are two processes: one being an optical process and the other using a magnetic substance. The present invention belongs to the latter class.

Heretofore, a magnetizable layer has been applied to a movie film by applying a dispersion of a magnetizable substance to a development-processed movie film. However, this process has the defect that since images are first recorded and then sound is recorded, images and sound cannot be recored at the same time. Therefore, with movie film having previously provided thereon a magnetizable layerit has been desired to remove the above-described defect, i.e.,-to enable one to record both images and sound at the same time.

On the other hand, in general, an antihalation layer is provided as a backing ,layer on a movie film, which antihalation layer can be removed with ease in the alkali development processing of the film.

In order to provide a magnetizable layer on a lightscnsitive movie film, it is necessary to apply a dispersion ofa magnetic substance onto the alkali-soluble antihalation layer provided as abacking layer. However, even when a normally employed dispersion of a magnetic substance is applied per se to the antihalation layer, the magnetizable layer formed is easily removed in the alkali development processing.

SUMMARY OF THE INVENTION The present invention relates to a process for strongly adhering a magnetizable layer to an antihalation layer on a movie film, where the antihalation layer at the portion on which the magnetizable layer has been coated is rendered insoluble in the alkali development processing used for such movie films, and to movie films thus produced.

According to the present invention, it has been found that in provided a magnetizable layer on a lightsensitive movie film, the magnetizable layer can be strongly adhered to the antihalation layer to the extent that the magnetizable layer is not removed in the development processing by applying a dispersion of a magnetic substance onto the antihalation layer after adding to the dispersion a compound having at least 2 isocyanato groups or thioisocyanato groups, or by previously processing the portion of the antihalation layer where the magnetizable layer is to be coated with a solution containing such a compound.

DETAILED DESCRIPTION OF THE INVENTION Preferred compounds within this class have from 2 to 4 isocyanato groups or thioisocyanato groups. This is because at the present time it is difficult to commercially obtain compounds have more than 4 isocyanato groups or thioisocyanato groups at reasonable cost.

As the binder for the antihalation layer, there are preferably used alkali soluble resins such as cellulose esters of dicarboxylic acids or vinyl copolymers containing maleic anhydride. Examples of cellulose esters of dicarboxylic acids are cellulose acetate phthalate, cellulose acetate maleate, hydroxyalkyl alkyl cellulose tetrahydrophthalate, hydroxyalkyl alkyl cellulose hexahydrophthalate (alkyl moiety thereof having from I to 4 carbon atoms and including a methyl, ethyl, propyl or butyl), and the like. Examples of vinyl copolymers containing maleic anhydride are maleic anhydride-styrene copolymers, maleic anhydride-styrene derivative c0- polymers, maleic anhydride-alkyl acrylate copolymers, maleic anhydride-alkyl methacrylate copolymers (alkyl moiety thereof having from 1 to 4 carbon atoms and including a methyl, ethyl, propyl and butyl groups), and the like. Examples of styrene derivatives include methylstyrene and p-chlorostyrene.

The dispersion for use in forming the antihalation layer suitable comprises 0.1 2% by weight of amixture of carbon black and the above described binder (mixing ratio: 10 parts by weight l5 50 parts by weight), balance organic solvent. The average particle size of the carbon black is preferably 20 30 mg.

In particular, the present invention is especially effective in the case wherein there is used, as the binder for the antihalation layer, a copolymer ofmaleic anhydride and styrene, a styrene derivative, an alkyl acrylate (alkyl moiety having 1 4 carbon atoms), an alkyl methacrylate (alkyl moiety having 1 4 carbon atoms) or the like, cellulose acetate phthalate, cellulose acetate maleate, hydroxyalkyl alkyl cellulose tetrahydrophthalate (alkyl moiety having I 4 carbon atoms), hydroxylakyl alkyl hexahydrophthalate (alkyl moiety having 1 4 carbon atoms), etc., with the copolymerization ratio of the vinyl copolymer containing meleic anhydride being 121, and preferred styrene derivatives including, for example, methylstyrene, pchlorostyrene, etc.

An antihalation layer to be provided on the surface of a photographic film opposite to the surface on which a light-sensitive silver halide emulsion layer is coated is designed to be alkali soluble. The antihalation layer is provided in order to prevent diffused reflection of incident rays upon photographing. The antihalation layer is designed so that it will be dissolved and removed in the step of photographic processing, particularly, development processing (the developer being alkaline). After such treatment, the film becomes transparent.

Therefore, if a magnetic recording layer is merely provided on the antihalation layer, the magnetic recording layer will be separated from the photographic film due to the removal of'the antihalation layer bonding both layers. For this reason, the antihalation layer is rendered alkali insoluble by adding a compound or compounds containing isocyanato groups or thioisocyanato groups to the magnetic recording layer, or, by processing before coating the magnetic recording layer, only the portion of the antihalation layer on which the magnetic recording layer is to be coated is rendered alkali insoluble.

The reason why the antihalation layer'is made insoluble in the alkali development processing by applying a dispersion of a magnetic substance after adding thereto a compound having two or more isocyanato groups or thioisocyanato groups, or by processing the portion of the antihalation layer on which portion the magnetizable layer is to be provided with a solution containing a compound having or more isocyanato groups or thioisocyanato groups, is considered to be that the applied compound diffuses into the antihalation layer and reacts with carboxyl groups present in the binder to form a two dimensional or three dimensional network structure in the binder. In general, the carboxyl groups are not in a salt form while contained in the antihalation layer, and are converted to a COOM (M alkali) type salt in alkali solution (i.e., upon development processing). As a result of this reaction, the antihalation layer becomes alkali soluble and is delaminated from the film. Therefore, carboxyl groups are not in a salt form before treating with an alkali solution.

Typical examples of the compound (or compounds, since mixtures can be used) used in the invention having at least 2 isocyanato groups or thioisocyanato groups are illustrated below.

Compound (I) OCN(CH )nI -ICO n=212,

Compound (H) C ompound (IX) C H:

Noo

OCN

Compound (X) a N C O wherein R represents a C C alkyl group, and Compound (XI) The amount of the compound (or compounds, since o 3 omNco,

Compound (VI) wherein the floating NCX group is located at the 0, m or p-position to R, X represents 0 or S, and R represents a hydrogen atom or a methyl group,

Compound (VII) (CH2) NC 0 H2) nNC 0 where n is 0 or 1,

Comfound Bi (V II) I 0 CN- H -N C 0 wherein Y represents a hydrogen atom or NCO, and R represents a hydrogen atom or mixture can be used) having isocyanato groups or thioisocyanato groups to the dispersion of magentic substance varies depending upon the kind of the compound, kind of the solvent for the dispersion, etc., i.e., compounds having a larger molecular weight are added in a greater amount, and compounds having less NCX groups in number are added in a greater amount (molar numbers). Further, the permeation speed of the solvent into the antihalation layer varies depending upon the combination of the binder used in the antihalation layer and the solvent. Where a solvent having a faster penetration speed is employed, the amount may be less since the isocyanato or thioisocyanato compound penetrates rapidly together with the solvent. However, the compound is preferably added to the dispersion of magnetic substance in an amount of 0.05% to 7% by weight, based on the total weight of the magnetic dispersion by weight).

Further, in the case of processing the antihalation layer prior to providing the magnetizable layer, it is desirable to conduct the processing with a solution containing 0.05% 10% (by weight) of the compound, based on the total weight of the coating solution by weight). Most preferably, the dried thickness of the magentic layer is about 7 to about 13 microns. The amount of compound in g/cm can be calculated from both the amount added to the magnetic dispersion and the thickness described above.

Where the antihalation layer is processed with a soluabout l5 to about 45 wt,

ferromagnetic powder(s) preferably 40 wt.7r,

binder about 5 toabout 20 wt.%,

preferably 7 20 wt.%, solvent about 35 to about 80 wt.7,

preferably 40 73 wt.7c.

The ferromagnetic powder can be yFe O y-Fe- 0 containing Co, Fe O Fe O, containing Co, CrO CO-Ni-Fe alloys or mixtures thereof, e.g., as described in Japanese Pat. Nos. 14090/69; 18372/70; 22062/72; 22513/72; 28466/71; 38755/71; 4286/72; 12422/72; 17284/72; 18509/72; 18573/72; and the like.

As the binder used for the recording layer in the present invention, a conventionally known thermoplastic resin, thermosetting resin, (or reaction-type resin) or mixtures thereof are used.

As the thermoplastic resins, those having a softening point of less than 150C, a mean molecular weight of about 10,000 to about 200,000 and a eopolymerization degree of about 400 to about 500, such as vinyl chloride-vinyl acetate copolymers, vinyl chloridevinylidene chloride copolymers, vinyl chlorideacrylonitrile copolymers, acrylate-acrylonitrile copolymers, acrylate-vinylidene chloride copolymers, acrylate-styrene copolymers, methacrylate-acrylonitrile copolymers, methacrylate-vinylidene chloride copolymers, methacrylate-styrene copolymers, urethane elastomcrs, nylon-silicone resins, nitrocellulose-polyamide resins, polyvinyl fluorides, vinylidene chlorideacrylonitrile copolymers, butadiene-acrylonitrile copolymers, polyamide resins, polyvinyl butyrals, cellulose derivativcs, styrene-butadiene copolymers, polyester resins, chlorovinyl ether-acrylate copolymers, amino resins, various synthetic rubber thermoplastic resins, and the like, are used.

Specific examples of such resins are illustrated in Japanese Pat. Nos. 6877/62; 12528/64; 19282/64; 5349/65; 20907/65; 9463/66; 14059/66; 16985/66; 6428/67; ll62l/67; 4623/68; 15206/68; 2889/69; l7947/69; 18232/69; 14020/70; 14500/70; 18573/72; 22063/72; 22064/72; 22068/72; 22069/72; 22070/72; 27886/72; and the like.

The thermosetting resin or reaction-type resin used preferably has a molecular weight of less than about 200,000 in the state of a coating solution and, upon heating after coating and drying, the molecular weight becomes infinite clue to the reaction of condensation, addition etc. Of these resins, those which are not softened or melted before the thermal condensation are preferred. To be specific, there are, for example, phenol resins, epoxy resins, polyurethane thermosettingtype resins, urea resins, melamine resins, alkyd resins, silicone resins, acrylic reactive resins, epoxy-polyamide resins, nitrocellulosemelamine resins, a mixture of a high molecular weight polyester resin and an isocyanate prepolymer, a mixture of a methacrylate copolymer and a diisocyanate prepolymer, a mixture of polyester polyol and a polyisocyanate, urea-formaldehyde resins, a mixture of a low molecular weight glycol/high molecular weight diol/triphenylmethane-isocyanate, polyamide resins and mixtures thereof.

Such resins are illustrated in Japanese Pat. Nos. 8103/64; 9779/65; 7192/66; 8016/66; l4275/66; 18179/67; l208l/68; 28023/69; l450l/70; 24902/70; 13103/71; 22065/72; 22066/72; 22067/72; 22072/72; 22073/72; 28045/72; 28048/72; 28922/72; and the like.

The magnetic recording layer is formed by dissolving the above-described composition in an organic solvent and applying the resulting coating solution to the antihalation layer. As the organic solvent used upon-coating, there can be employed ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, etc., alcohols such as methanol, ethanol, propanol, butanol, etc.; esters such as methyl acetate, ethyl acetate, butyl acetate, propyl acetate, amyl acetate, ethyl lactate, glycol acetate, monoethyl ether, etc.; ether; glycol ethers such as glycol dimethyl ether, glycol monoethyl ether, dioxane, etc.; aromatic hydrocarbons such as benzene, toluene, xylene, etc.; chlorinated hydrocarbons such as methylene chloride, ethylene chloride, carbon tetrachloride, chloroform, trichloroethane, ethylene chlorohydrin, dichlorobenzene, and the like.

Any of the solvents used to form the magnetic layer can also be used as solvents in the case where the com pound having at least two isocyanato or thioisocyanato groups is directly applied to the antihalation layer. As the preferred solvents used, there are ketones, e.g., acetone, methyl ethyl ketone, cyelohexanone, etc., esters, e.g., methyl acetate, ethyl acetate, propyl acetate, butyl acetate, amyl acetate, etc., chlorinated hydrocarbons, e.g., methylene chloride, ethylene chloride, trichloroethane, etc., dioxane, tetrahydrofuran, morpholine, dimethylformamide, methyl cellosolve acetate, aromatic hydrocarbon such as benzene, toluene and xylene and the like, used alone or in suitable combinations.

The solvent used can vary depending upon the binder for the the dispersion of the magnetic recording layer, the binder for the antihalation layer and the isocyanato or thiosocyanato compounds. However, a proper solvent can be selected with ease by a person skilled in the art the following points in mind:

1. the solvent should dissolve the binder for the magnetic recording layer;

2. the solvent should dissolve the isocyanato or thioisocyanato compound;

3. the solvent should dissolve or swell the binder for antihalation layer; and

4. the solvent should not react with the compounds or components described in the above articles (1) (3).

In addition, the solvent should be selected considering a boiling point, etc., suitable for the coating or drying process.

The present invention will now be illustrated in more detail by several non-limiting examples of preferred embodiments of the invention. Solution compositions in the example are expressed in terms of parts by weight.

All movie film in the Examples comprised standard gelatino silver halide light sensitive emulsions for use in color photography coated on the side of the support opposite the antihalation layer and magnetic recording layer.

EXAMPLE 1 and dried at 100C for 10 minutes to form an antihalation layer.

Copolymer between styrene and maleic anhydride (1:1 molar ratio) 10 Carbon black (20 30 mp particle size) 5 Methanol 40 Acetone 60 The polycondensation ester had the following composition. A polyester was formed by adding an ester exchange reaction catalyst to a mixture of 1 mol. of dimethyl terephthalate, 1.7 moles of ethylene glycol, and 0.8 mol of triethylene glycol.

The cellulose ester was cellulose triacetate. The mixture for subbing layer has the following composition. Into a mixed solvent of 52 parts of ethylene dichloride, 8 parts of methylene chloride, 20 parts of methanol, 20 parts of tetrachloroethane and 20 parts of phenol were dissolved 0.2 part of the above-prepared polyester and 0.2 part of the cellulose triacetate, and the coating solution was applied to the surface of the polyethylene terephthalate film at 80C. and dried for 6 minutes at 100C. The procedure is in accordance with Example 1 of U.S. Pat. No. 3,492,122.

To the antihalation layer thus formed on the lightsensitive movie film for use in color photography there was applied a dispersion of a magnetic substance having the following composition which was then dried at 40C for 3 minutes.

Nitrocellulose (M.W. ca 70000-80000) Ferromagnetic 'y-Fe O (average particle size: 08 X 0.1 -X 0.1 micron) 30 Dibutyl phthalate 2 Ethyl acetate Butyl acetate Cellosolve acetate 10 Compound (1V) 0.5

When the resulting movie film having thereon the resulting magnetizable layer (ca 840 1. thick) was subjeeted to standard color development processing, i.e.,

EXAMPLE 2 A solution having the following composition was applied to the antihalation layer of a light-sensitive movie 5 film as in Example 1 having the same antihalation layer as in Example 1, and dried at C for 3 minutes.

Nitrocellulose (M.W. ca (10000-80000) 2 H Acetone 40 Butyl acetate 30 Dioxane 30 Compound (V) Subsequently, a dispersion of a magnetic substance having the following composition was applied thereto and dried at 50C for 3 minutes. Too high a temperature or too long a drying time exerts a detrimental influ- 20 ence on the photographic emulsion layer and is therefore not favorable. Preferable ranges are about 30 60C in temperature and about 2 20 minutes in drying time.

sulting magnetizable layer (ca 8 10p. thick) was alkali-processed as in Example 1 and used in a projector equipped for magnetically recording and reproducing sound and projecting repeatedly 200 times, no damage 40 was observed in the magnetizable layer.

EXAMPLE 3 An antihalation layer was formed on a light-sensitive movie film for color photography comprising a cellulose triacetate support by applying a solution having composition (A) and drying the same. Then, a dispersion of a magnetic substance containing different compounds having isocyanato groups or thioisocyanato groups as shown by composition (B) was applied and dried at 40C for 3 minutes.

Composition (A) Hydroxymethyl methyl cellulose tetrahydrophthalate 10 Carbon black (20 30 my. particle size) 5 Acetone 70 Methanol 30 Composition (8) Nitrocellulose (MW ca 50,000 80,000) 10 0 lron oxide (same as in Example 1) 30 dibutyl phthalate 2 lsoamyl acetate 20 Acetone 20 Dioxane 20 The results obtained by subjecting the resulting films toalkali development processing as in Example 1 were as follows.

dclaminated during develop ment processlng.

While the invention has been described in detail and with reference to specific embodiments thereof, it will be apparent to one skilled in the art that various changes and modifications can be made therein without departing from the spirit and scope thereof.

What is claimed is:

l. A process for producing a photographic film having thereon a magnetic recording layer by applying a dispersion of a magnetic substance to an antihalation layer of a llght-sensitive film for cinema. wherein the dispersion contains a compound or compounds, having at least two isocyanato groups or thioisoeyanato groups capable of rendering said antihalation layer alkali insoluble, thereby rendering said antihalation layer alkali insoluble.

2. The process as claimed in claim I wherein said dispersion of magnetic substance comprises from about 15 to about 45% by weight of ferromagnetic powder, from about 5 to about 20% by weight of binder, and from about 35 to about 80% by weight of solvent.

3. The process as claimed in claim 2 wherein said dispersion contains 0.05 to 7% by weight, based on said dispersion, of said compound.

4. The process as claimed in claim 1 wherein said compound has from 2 to 4 isocyanato groups or thioisoeyanuto groups.

5. The process as claimed in claim 4 wherein said compound is selected from the group consisting of Compounds (l) to (Xl) below:

Compound (I) V T7VLV=2V;12,

command (n o ei:r o1i; mX(oH2) NCO X=O or s,

Compound (III) SCN(CH2)nNCS n=2-10,

Compound (IV) (13H; (3H3 O CNCHZ-(J-OH2-CHCHZCH2NC 0,

Compound '(v CH3 7 M GET:

CH: omNoo,

Compound (VI) NCX l NCX (CHZMNOO Hz),.NCO

Compound (VII) where n is 0 or 1,

Compound 0 CN H NC 0 represents a hydrogen atom or wherein the floating NCX group is located at the 0am: or p-position to R, X represents 0 or S, and R repre sents a hydrogen atom or a methyl group,

C Ha

Compound (IX) OCN NCO CHa- -CH:

NCO

Compound (X) C O wherein R represents a C C alkyl group, and

OCN NCO NCO NCO 6. The process as claimed in claim 1 wherein said magnetic recording layer has of from about 7 to about 13 microns of a dried thickness.

7. The process as claimed in claim 1 wherein said solution contains from 0.05 to 10% by weight, based on total weight of said solution, of said compound.

8. The process as claimed in claim 7 wherein the dried thickness of said processing solution is from about one-tenth to about one-fiftieth of the dried thickness of said magnetic recording layer.

9. A motion picture film having a magnetic recording layer coated on the antihalation layer coating on the film support at the the opposite side of the light sensitive photographic layer, said magnetic recording layer comprising a compound having at least two or more isocyanato groups or thioisoeyanato groups capable of and thereby rendering said antihalation layer alkali insoluble.

10. The motion picture film as claimed in claim 9 wherein said magnetic recording layer is coated from a dispersion of the magnetic substance, which comprises from about 15 to about 45% by weight of ferro magnetic powder, from about 5 to about 20% by weight of binder, and from about 35 to about by weight of solvent.

11. The motion picture film as claimed in claim wherein said dispersion contains from 0.05 to 7% by weight, based on said dispersion, of said compound.

12. The motion picture film as claimed in claim 9 wherein said compound has from 2 to 4 isocyanato groups or thioisocyanato groups.

13. The motion picture film as claimed in claim 12 wherein said compound is selected from the groups consisting of Compounds (1) to (Xl) below:

wherein the floating NCX group is located at the o-, mor p-position to R, X represents 0 or S, and R represents a hydrogen atom or a methyl group,

Compound whore 7L is 0 or 1,

Compound (VIII) wherein Y represents a hydrogen atom or NCO, and R represents a hydrogen atom or Compound (IX) Compound (X) wherein R represents a C, C alkyl groups, and 7 Compound 7 OCN if CH3 CH2 CH3 NCO NCO r iiim'ofibn picture film haying a" magneticrecording layer, a subbing layer, and an antihalation layer coated on the film support on the opposite side of the light sensitive photographic layer, said subbing layer comprising a compound having at least two or more isocyanato groups or thioisocyanato groups capable of rendering said antihalation layer alkali insoluble and being in contact with said antihalation layer, thereby rendering said antihalation layer alkali insoluble.

15. A motion picture film claimed in claim 14 wherein said compound has from 2 to 4 isocyanato groups or thioisocyanato groups.

16. A motion picture film claimed in claim 15 wherein said compound is selected from the group consisting of Compounds (1) t0 (XI) below:

Compound (I) OQN(CH2)11NCO n=212,

Compound (II) 0ON(CH2)m' X (CH2)DNCO X=O or S,

Compound (III) SCN(CHZ)nNCS n=210,

Compound (IV) (ll'Ha CH:

0 ONCH:$CHr-CH*CH2CH2NC 0,

Compound (v GHa M v NCO C a CH2NCO,

Compound (VI) NCX I NCX wherein the floating NCX group is located at the 0-, mor p-position to R, X represents 0 or S, and R represents a hydrogen atom or a methyl group,

Compound in cuonNoo where n is 0 or 1,

Com ound Bi (V II) (13 wherein Y represents a hydrogen atoiiir and R represents a hydrogen atom or Compound (IX) Compound (X) wherein R represents a C C alkyl group, and

Compound (XI) CN NC 0 NCO N00 17. A process for producing a photographic film having thereon a magnetic recording layer by applying a dispersion of a magnetic substance to an antihalation layer of a light-sensitive film for cinema, wherein the antihalation layer is processed with a solution containing a compound or compounds having at least two isocyanato groups or thioisocyanato groups capable of rendering said antihalation layer alkali insoluble before application of said dispersion, thereby rendering said antihalation layer alkali insoluble.

18. The processas claimed in claim 17 wherein said dispersion of magnetic substance comprises from about l5 to about 45% by weight of ferromagnetic powder, from about 5 to about by weight of binder, and from about to about 80% by weight of solvent.

19. The process as claimed in claim 17 wherein said compound has from 2 to 4 isocyanato groups or thioisocyanato groups.

20. The process as claimed in claim 19 wherein said compound is selected from the group consisting of Compounds (l) to (Xl) below:

NCX

| NCX Compound (VI) wherein the floating NCX group is located at the o-, mor p-position to R, X represents 0 or S, and R represents a hydrogen atom or a methyl group,

Compound (CH2) n 0 JH2)aNCO where n is 0 or 1,

Compound R1 (VIII) i 0 CN 11- NC 0 wherein Y represents a hydrogen atom or NCO, and R represents a hydrogen atom or Compound (X) NC 0 wherein R represents a C. alkyl group, and

Compound (XI) 0 C N N C O 21. The process as claimed in claim 17 wherein said magnetic recording layer has of from about 7 to about 13 microns of a dried thickness.

UNITED STATES PATENT OFFICE CERTIFICATE OF CORRECTION PATENT NO. 1 3,870,525 DA March 11, 1975 INVENTOR(S) Nobuo YAMAMOTO et a1 It is certified that error appears in the above-identified patent and that said Letters Patent are hereby corrected as shown below:

IN THE HEADING:

Foreign Application Priority Data Delete "Apr. 12, 1972" insert --Apr. 24,1972 Q...

Signed and sealed this 20th day of May 1975.

(SEAL) Attest:

C. MARSHALL DANN RUTH C. MASON Commissioner of Patents Attesting Officer and Trademarks 

1. A process for producing a photographic film having thereon a magnetic recording layer by applying a dispersion of a magnetic substance to an antihalation layer of a light-sensitive film for cinema, wherein the dispersion contains a compound or compounds, having at least two isocyanato groups or thioisocyanato groups capable of rendering said antihalation layer alkali insoluble, thereby rendering said antihalation layer alkali insoluble.
 1. A PROCESS FOR PRODUCING A PHOTOGRAPHIC FILM HAVING THEREON A MAGNETIC RECORDING LAYER BY APPLYING A DISPERSION OF A MAGNETIC SUBSTANCE TO AN ANTIHALATION LAYER OF A LIGHTSENSITIVE FILM FOR CINEMA, WHEREIN THE DISPERSION CONTAINS A COMPOUND OR COMPOUNDS, HAVING AT LEAST TWO ISOCYANATO GROUPS OR THIOSOCYANATO GROUPS CAPABLE OF RENDERING SAID ANTIHALATION LAYER ALKALI INSOLUBLE, THEREBY RENDERING SAID ANTIHALATION LAYER ALKALI INSOLUBLE.
 2. The process as claimed in claim 1 wherein said dispersion of magnetic substance comprises from about 15 to about 45% by weight of ferromagnetic powder, from about 5 to about 20% by weight of binder, and from about 35 to about 80% by weight of solvent.
 3. The process as claimed in claim 2 wherein said dispersion contains 0.05 to 7% by weight, based on said dispersion, of said compound.
 4. The process as claimed in claim 1 wherein said compound has from 2 to 4 isocyanato groups or thioisocyanato groups.
 4. THE PROCESS AS CLAIMED IN CLAIM 1 WHEREIN SAID COMPOUND HAS FROM 2 TO 4 ISOCYANATOR GROUPS OR THIOSOCYANATO GROUPS.
 5. THE PROCESS AS CLAIMED IN CLAIM 4 WHEREIN SAID COMPOUND IS SELECTED FROM THE GROUP CONSISTING OF COMPOUNDS (I) TO (X) BELOW: COMPOUND (I) OCM(CH2)NNCO N=2 - 12, COMPOUND (II) OCN(CH2)M-X-(CH2)NNCO X=0 OR S, COMPOUND (III) SCN(CH2)NNCS N=2 - 10, COMPOUND (IV)
 5. The process as claimed in claim 4 wherein said compound is selected from the group consisting of Compounds (I) to (XI) below:
 6. The process as claimed in claim 1 wherein said magnetic recording layer has of from about 7 to about 13 microns of a dried thickness.
 7. The process as claimed in claim 1 wherein said solution contains from 0.05 to 10% by weight, based on total weight of said solution, of said compound.
 8. The process as claimed in claim 7 wherein the dried thickness of said processing solution is from about one-tenth to about one-fiftieth of the dried thickness of said magnetic recording layer.
 9. A motion picture film having a magnetic recording layer coated on the antihalation layer coating on the film support at the the opposite side of the light sensitive photographic layer, said magnetic recording layer comprising a compound having at least two or more isocyanato groups or thioisocyanato groups capable of and thereby rendering said antihalation layer alkali insoluble.
 10. The motion picture film as claimed in claim 9 wherein said magnetic recording layer is coated from a dispersion of the magnetic substance, which comprises from about 15 to about 45% by weight of ferromagnetic powder, from about 5 to about 20% by weight of binder, and from about 35 to about 80% by weight of solvent.
 11. The motion picture film as claimed in claim 10 wherein said dispersion contains from 0.05 to 7% by weight, based on said dispersion, of said compound.
 12. The motion picture film as claimed in claim 9 wherein said compound has from 2 to 4 isocyanato groups or thioisocyanato groups.
 13. The motion picture film as claimed in claim 12 wherein said compound is selected from the groups consisting of Compounds (I) to (XI) below:
 14. A motion picture film having a magnetic recording layer, a subbing layer, and an antihalation layer coated on the film support on the opposite side of the light sensitive photographic layer, said subbing layer comprising a compound having at least two or more isocyanato groups or thioisocyanato groups capable of rendering said antihalation layer alkali insoluble and being in contact with said antihalation layer, thereby rendering said antihalation layer alkali insoluble.
 15. A motion picture film claimed in claim 14 wherein said compound has from 2 to 4 isocyanato groups or thioisocyanato groups.
 16. A motion picture film claimed in claim 15 wherein said compound is selected from the group consisting of Compounds (I) to (XI) below:
 17. A process for producing a photographic film having thereon a magnetic recording layer by applying a dispersion of a magnetic substance to an antihalation layer of a light-sensitive film for cinema, wherein the antihalation layer is processed with a solution containing a compound or compounds having at least two isocyanato groups or thioisocyanato groups capable of rendering said antihalation layer alkali insoluble before application of said dispersion, thereby rendering said antihalation layer alkali insoluble.
 18. The process as claimed in claim 17 wherein said dispersion of magnetic substance comprises from about 15 to about 45% by weight of ferromagnetic powder, from about 5 to about 20% by weight of binder, and from about 35 to about 80% by weight of solvent.
 19. The process as claimed in claim 17 wherein said compound has from 2 to 4 isocyanato groups or thioisocyanato groups.
 20. The process as claimed in claim 19 wherein said compound is selected from the group consisting of Compounds (I) to (XI) below: 